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A peaceful Hamptons neighborhood nestled on the North Fork of eastern Long Island, the exquisite Southold hamlet invites residents to enjoy wide-open farmland and small-town charms from antique shops to roadside produce stands. Established in 1640 as New York’s oldest English settlement, Southold continues to evolve today.

Dotted with acres of open farmland, world-renowned vineyards, and ample space devoted to public parks, the delightful community with a rich heritage continues to thrive with unique shopping opportunities, top casual and fine dining fare, historic buildings, beautiful museums, and unlimited recreational opportunities.

Its countrified qualities, culture, and history make Southold a special place to live, especially for those who prefer homes set on well-tended acres of farmland rather than tracts best measured by the square foot. Southold is a nirvana for residents who prefer natural island beauty over suburban life or summer hotspot festivities.

The hamlet of Cutchogue is home to not just Long Island’s first winery (established in 1973) but also one of best surviving examples of domestic English architecture in the United States. Peconic—named for Peconic Bay and once home to Albert Einstein—has roots as a noted artists’ haven dating back to the early 20th century.

Walk the unspoiled beaches along the Long Island Sound and Noyack Bay, rich with stretches of pristine sand. Known for its wine culture, Southold’s North Fork features sprawling vineyards and wineries open year-round for tours and tastings. Also part of the township are Robins Island, Plum Island, and Fisher’s Island.

Contact Team Rita today to schedule viewings for homes in Southold, New York. Call to schedule a free consultation with one of our real estate agents.


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  1. 4 Beds,  2 Baths
    1,500 sqft  
    MLS 804563
    4 Days on Market
  2. 3 Beds,  2 Baths
    lot 5,663 sqft
    MLS 806303
    5 Days on Market
  3. 2 Beds,  2 Baths
    1,300 sqft  
    MLS 804495
    11 Days on Market
  4. 2 Beds,  1 Bath
    1,400 sqft   lot 9,584 sqft
    MLS 806218
    11 Days on Market
  5. 3 Beds,  3 Baths
    1,100 sqft   lot 43,560 sqft
    MLS 804899
    11 Days on Market
  6. 0 Beds,  3.5 Baths
    1,860 sqft   lot 19,602 sqft
    MLS 804042
    16 Days on Market
  7. 4 Beds,  2.5 Baths
    3,400 sqft  
    MLS 802824
    18 Days on Market
  8. 3 Beds,  2.5 Baths
    1,580 sqft   lot 9,584 sqft
    MLS 802131
    19 Days on Market
  9. 6 Beds,  5.5 Baths
    3,630 sqft   lot 21,650 sqft
    MLS LP1439478
    26 Days on Market
  10. 4 Beds,  2 Baths
    1,520 sqft   lot 6,055 sqft
    MLS L3593108
    26 Days on Market
  11. 1 Bed,  1 Bath
    896 sqft   lot 8,059 sqft
    MLS L3592990
    27 Days on Market
  12. 3 Beds,  2 Baths
    1,900 sqft   lot 13,548 sqft
    MLS L3592877
    29 Days on Market
  13. 4 Beds,  5.5 Baths
    4,671 sqft   lot 43,299 sqft
    MLS L3592723
    30 Days on Market
  14. 4 Beds,  3 Baths
    1,800 sqft   lot 39,814 sqft
    MLS L3592550
    31 Days on Market
  15. 4 Beds,  3.5 Baths
    3,500 sqft   lot 25,091 sqft
    MLS L3592616
    31 Days on Market
  16. 4 Beds,  2 Baths
    2,200 sqft   lot 3.19 ac
    MLS L3592218
    32 Days on Market
  17. 3 Beds,  1 Bath
    1,277 sqft   lot 12,546 sqft
    MLS L3592192
    32 Days on Market
  18. 5 Beds,  3.5 Baths
    2,600 sqft   lot 15,595 sqft
    MLS L3591501
    38 Days on Market
  19. 3 Beds,  2.5 Baths
    1,872 sqft   lot 21,650 sqft
    MLS L3590647
    40 Days on Market
  20. 4 Beds,  2.5 Baths
    1,800 sqft   lot 38,115 sqft
    MLS L3590576
    40 Days on Market
  21. 4 Beds,  3.5 Baths
    4,400 sqft   lot 1.00 ac
    MLS L3590402
    41 Days on Market
  22. 5 Beds,  3 Baths
    lot 26,833 sqft
    MLS L3590333
    42 Days on Market
  23. 5 Beds,  4.5 Baths
    2,950 sqft  
    MLS H6335251
    43 Days on Market
  24. 4 Beds,  6 Baths
    5,220 sqft   lot 14,811 sqft
    MLS L3590145
    44 Days on Market
  25. 3 Beds,  1.5 Baths
    2,000 sqft   lot 1.74 ac
    MLS L3590177
    44 Days on Market
  26. 11 Beds,  13 Baths
    lot 131 sqft
    MLS L3590171
    44 Days on Market
  27. 2 Beds,  1 Bath
    MLS L3589570
    46 Days on Market
  28. 3 Beds,  2.5 Baths
    lot 2.03 ac
    MLS L3588159
    55 Days on Market
  29. 3 Beds,  2 Baths
    1,300 sqft   lot 5,925 sqft
    MLS L3587738
    56 Days on Market
  30. 5 Beds,  4.5 Baths
    4,627 sqft   lot 42,864 sqft
    MLS L3587614
    57 Days on Market
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